A Challenging New Riddle
by author422
Summary: What if Tom Riddle never became Voldemort? What if Tom Riddle never killed his parents and grandparents? What if he never set a basilisk on Muggleborns in Hogwarts? What if, just what if, Tom Riddle fell in love?
1. Chapter 1

AN: I know you all were looking forward to an update on the Harry Potter and the Twinkle-Eyed Headmaster series, but I have too many ideas littered around in my brain. I just _had_ to get this one out, because I love Tom Riddle fanfics, except if they're too mushy. Come on; this is the guy who would've turned into Voldemort, for Moody's sake! I hope you sincerely, well, maybe not _like, _but appreciate this fanfic.

Disclaimer: I don't own Harry Potter in any way, shape, or form.

Chapter 1- In Which Luna Gets Thrown Into The Past

Tom Riddle was having a perfectly fine day. Well, there was that unfortunate start at the orphanage, like every summer. But now that he was on the Hogwarts Express, everything seemed to take a turn for the better. Of course, his good mood didn't have anything to do with the fact that he was going home. His _real_ home, Hogwarts School of Witchcraft and Wizardry, which was where he had discovered his heritage. A rather fine one too; he was the last living descendent of Salazar Slytherin, which was practically like royalty to him!

He looked out of the window of the train compartment he was in. Trees and various shrubbery rushed by in a blur, as the train gained speed, while leaving the magical station hidden behind a pillar on the Muggle station. Tom was alone in his compartment. He always was. Oh, there were always people who wanted to sit with him: giggling fan-girls, and adoring, awe-filled Slytherins. But Tom liked to be by himself usually, for that was how he had been brought up. Anyhow, who needed one's company, when you could enjoy peace and quiet? Besides, people spoke about the most mundane and un-interesting things nowadays, like who was going out with whom. _Honestly_, thought Tom, _their lives are so pathetic that they have to criticize others' lives._

* * *

Luna was waiting in Professor Dumbledore's office patiently. She sighed; the bullying in the Ravenclaw girl dormitories had become unbearable. It wasn't even worth hiding behind her Nargles facade. Her year-mates just mocked her even more when she did that. Absentmindedly, she picked at a loose thread on her Ravenclaw tie. She never understood completely on why nobody liked her. She had no friends other than Ginny Weasley, who was very nice, but Ginny was in Gryffindor, quite far from the Ravenclaw tower. Besides, Luna never liked to depend on anybody when it came to _this_. It was personal, and like admitting to everyone that she was pathetic, that she _was_ strange.

Luna sighed in weariness. Sooner or later, Professor Dumbledore would find out. And he did. _It was a bit of a relief_, she supposed. _I do wish though, that he had refrained from leaving me in his rather interesting office. He does know I am a Ravenclaw, and a rather curious one, at that? _Fawkes was nowhere to be seen, as she looked around. A pang of sadness echoed in her heart. She couldn't help but think that even Fawkes wanted to leave her alone. It was then that Luna noticed a shiny, golden timepiece on Professor Dumbledore's desk. She bit her lip in hesitation. _It was like it was calling out to her. _She wanted to pick it up so bad. Luna looked back at the door. She had absolutely no idea that pair of dark, beady eyes was focused on her. The pair of eyes belonged to a bird, with magnificent crimson-golden plumage. He was hidden among his master's bookshelves, among some thickly bound, scarlet journals, that had golden script written on their spines.

Luna looked back towards the gleaming timepiece that was begging for her to touch it. It beckoned invitingly, and Luna had no choice but to follow her heart's instinct on this. This was an impossibly cliché thing to say, but Luna sometimes did cliché things. Swallowing nervously, pushing the knot of anxiety that had formed in her throat, she shuffled forward to Professor Dumbledore's desk. Holding her breath in fascination, she slowly stretched out her index finger, and lightly drew her finger across the shining surface. She had only a millisecond of having a feeling of satisfying her curiosity, before she vanished with a POP!

Fawkes trilled once, a long piercing sound directed near the door. A moment later, Professor Dumbledore emerged, his image rippling, as the Disillusionment Charm he had on was taken off. His merry blue eyes twinkled, and he hid a smile under his snow-white beard. "I agree, Fawkes, my friend. I'm sure dear Luna will be in perfectly capable hands. She'll have a better life then, than she does now."

* * *

POP! Tom jumped out of his seat, and the book he was reading flew out of his hands and onto the person's head. Wait…what? Tom looked over at the girl who had, amazingly, popped into his compartment. He immediately found himself studying her. She had luminescent blonde hair, but it wasn't silver, it was… He didn't actually know. Tom was quite sure that her hair color didn't exist, or that it was quite rare. Her eyes, as they peered up at him in shock, were a sapphire blue, and he was momentarily entranced by them. He had never seen anything look so, so… _blue_.

Luna, meanwhile, was examining him as well. She recognized him as Tom Riddle of course. She supposed that the rumors were slightly true, at least. He was…what did the other girls say? Ah yes, of course. _Handsome_. She didn't have any experience on that matter of course; nobody was her friend, other than Ginny, and she had a rather large crush on Harry Potter. Luna vaguely wondered if it was even a crush anymore. Not really, she guessed. Ginny's feelings had developed into love and for the real Harry too. _Well_, she mused, _this leaves me in a bit of a predicament. I'm stuck in a train compartment on what is obviously the Hogwarts Express, with Tom Riddle. My fifth year has gone off to a fabulous start, and classes haven't even started yet. _

Luna noticed that Tom's eyes were still trained on her, as if he found her surprising and a bit unnerving. It wasn't an unfamiliar look. People looked at her like that all the time. Still, it irked her a bit. Calmly, while putting a bit of her dreamy tone into it, she asked politely, "What year is it?" Tom's brows furrowed in confusion, but his eyes lit up with interest. "1942," he answered just as politely, though rather coolly. After all, he wasn't in Slytherin for nothing. He gazed at the intruder distastefully. "Are you pureblooded?" he asked suddenly. Luna peered at him, with a strange emotion on her face. Tom realized that it was disappointment, but kept an aloof disposition, as he waited for her answer.

Luna thought to herself, _I knew he'd ask that. Why on earth am I feeling a bit disappointed? _She answered just as coolly, "Yes, but I don't see how that matters." She saw his eyes sharpen a bit. "So you're a blood-traitor," he stated in plain disgust. Luna raised an eyebrow. Clearly, he was the perfect Slytherin from back home. If it wasn't for his name, the date, and his looks, Luna would swear that he was related to Draco Malfoy. She retorted back coldly, "I don't believe in scorning others for something they had no control over, Tom." _Bullseye_.

Tom's eyes widened, unable to control himself. _How-how did she-? _Did she_ know? _Tom leaned back in his seat, and his sudden movement startled Luna, which he smirked at. Luna gazed steadily back at him, before picking herself off the floor, and sitting across from him, much to his frustration. Unable to handle her silence and the fact that she continued to sit there, he tried to give her a hint, with just a tint of a demand in his voice. "I like to sit alone during train rides." _Alright, so that was too much of a hint, but so what? Maybe she would finally leave him alone after that_. He watched her turn her penetrating gaze to him, which eerily reminded him of Dumbledore, the old fool.

Luna opened her mouth finally to say something. "Do you? I suppose we have something in common, in a way." Tom raised his eyebrows in a gesture for her to explain. And explain she did. "People don't like to sit with me, mostly because they think that I am so unusual. I'm rather used to it. Although, I imagine it's the other way around for you." Tom mulled over the new information in his head. Yes, he could see why nobody would want to sit with her. _Honestly, who wears radish earrings with a butterbeer bottle-cap necklace? _he mentally wondered. He voiced the thought aloud to her. "Well, _normal_ people don't go around wearing radishes as earrings." Seeing the girl wince, he smirked smugly to himself. It appeared that he had hit a nerve. A moment of silence passed, before a soft voice said quietly, sadly, "They were from my mother."

Tom caught the hidden use of past-tense in her words. _So, her mother's dead. Well, way to make pureblood connections, Tom_, he mentally scolded himself. But really, who cared? After all, _his_ mother died, and you didn't see him going all soft-voiced, trying to gain pity from people. No; Tom Marvolo Riddle was much cleverer than that. Luna caught his sneer of disgust in his eyes. Their eyes were locked on each other's, chocolate brown meeting sapphire blue. She gazed at him for a moment, before turning away, seeming to have little interest in him.

Tom's brows furrowed once more, this time in thought. The girl across from him was very peculiar. She was obviously not from this time period; her clothes made him certain of that. The fact that she had also asked for the year just made it more concrete. He was positively _itching_ to ask her questions about the future, but shoved the urge in, and calmed himself. After all, this sort of thing meant that you had to gain the person's complete and absolute trust, before trying anything. Tom was very talented at this skill. Some called this skill manipulating, but Tom called it Smart Arts. Alright, he wasn't good at making up names, but there was no need to snicker.

Luna got up, when the trolley lady swung by their compartment. "Anything from the trolley, dears?" she asked. Tom shook his head firmly, a silent _No_. Luna was just coming back, holding a Cauldron Cake, when…

BUMP. The train jolted a little, causing her to lose her balance. Her Cauldron Cake that she was holding, flew right out of her hands, and landed in her seat. She, herself, however, began to fall…right onto a very warm body. Her eyes were shut tightly, and slowly, she opened them, only to come face-to-face with Tom Riddle's chocolate brown eyes. They held no emotion within, although Luna was sure that she saw a flicker of concern in them. Luna didn't know if Tom Riddle was strong or not, because Luna weighed very little, only eighty pounds. All she knew that a pair of arms was encircled around her, not letting her fall to the floor. _It was a good thing that he had caught me, otherwise I might've gotten a concussion or something equally painful_, mused Luna.

Carefully, she untangled herself from him, and went back to her seat, smoothing down her robes as she sat down. She looked up at Tom, who was watching her in surprise. _No doubt that he's had very different reactions with other girls_, thought Luna in amusement. She nodded politely in his direction, and said softly, "Thank you, Tom." She could only watch in amusement as he turned away from her, the only sign of acknowledgement of her 'thank-you' being his pink cheeks, and a mumbled, "You're welcome."

AN: So…any good? On this fanfic, I really need reviews. I'm going to be a review-holic here. Sorry guys, but this will be helping me with one of my real stories that I'm writing. Please review. And I know there's a picture of Tom as the cover, but to see how he really looks in this story, you'll have to look up 'Gryffindor Tom Riddle'. There should be a Google image of him that pops up with a normal him, and then a Gryffindor him. Once again, please review. Oh, and a _REALLY_ good Tom Riddle fanfic would be Have I Ever by Lady Moonglow.

Watch out for Nargles,

:) author422


	2. Chapter 2

AN: Since I have instantly got some positive reviews, just barely after I put my story up, I decided to update another chapter today. Of course, that _might_ mean the Harry Potter and the Twinkle-Eyed Headmaster series might be put on hold. I'm truly sorry to my reviewers and readers alike, if that's the case. I WILL NOT abandon it; I never abandon a story or my characters. Chapters for that series might be slow-coming, that's all. :'( I really don't want to stop the series, and I promise you that I won't. But having a continuously active imagination, means I have to continuously start new stories, or at least write summaries of them, so I won't forget them. I hope you can forgive me in due time.

Disclaimer: I don't own Harry Potter in any way, shape, or form.

Chapter 2- In Which Tom Sees Luna's Second Most Private Memory

Luna fiddled with her long black sleeve of her robe. Apparently, she would have to find a way to get to Professor Dumbledore, and perhaps pose as a transfer student. _Something of the sort will have to do_, she thought absentmindedly. Luna hesitantly glanced at Tom, or rather, his back. She had nothing with her that she brought, but she was reminded that it was September 1st, and the start of the school year, as Tom easily lifted his trunk from above his seat, and setting it on the floor. _He _is_ strong_, mused Luna. _Guess I was right. I bet my dorm mates would love to know that fact. _Luna snorted to herself, not knowing she had caught Tom's attention. _Girls these days,_ she thought exasperatedly. _They care about the most useless things._

Tom was a master at Legilimency. As a matter of fact, he was the youngest in over a century, which had slightly boosted up his ego, when he read about it in the library. The nice thing about it was that his probes were so gentle, that it was impossible for people to know when he had looked in their heads. So when he heard the snort from the other inhabitant of _his_ compartment, his curiosity overwhelmed him, and he decided to take a peek into her mind. _A quite interesting mind, too_, was the first thought that rang throughout his head. Memories floated around in the girl's mental being, and little tidbits of information passed Tom by, such as where to find a Crumple-Horned Snorkack.

Tom blinked in bemusement. _Crumple-what?_ _What on earth is that? Does that even exist?_ Thinking back to the words she had spoken about sitting alone, he suddenly understood. _It was probably a made-up creature of hers_, he sneered mentally. Shaking his head, he searched through her head. He had no idea that her wide, innocent, sapphire eyes were staring at him willingly.

Oh yes, Luna knew he was in her head. It was quite obvious, really, that he would try sooner or later. She didn't try to hide the fact that she was from the future, after all. Luna mentally pulled forth memories that wouldn't cause any harm by letting him look at them. Luna suddenly had a _grand_ idea. Mentally smirking in glee, she pulled forth a memory of her last time in Hogwarts, in the Ravenclaw girls' dormitory. Maybe he would finally see that this was why she didn't sneer down on others. Luna thought mournfully, _Oh, I wish I had a camera…_

Tom watched in surprise, as one of the memories whirling around him, pushed forward to the front, as if begging to be watched. Tom was slightly giddy. _This is a treasure trove of blackmail_, he thought. Tom cautiously looked around at the other memories that were pushing the other for the front. Smiling wickedly, thinking he would be here for a while, he settled down on the imaginary floor beneath him, criss-crossing his legs, and making himself comfortable.

Tom Marvolo Riddle didn't have an inkling of what he would be seeing, but what he would see would always be etched in his mind.

_A girl Tom recognized as the girl who had popped into his compartment, was sitting on the edge of a four-poster bed, the silky blue hangings drawn apart. The windows that offered an amazing view of the distant mountains, and the Black Lake, also showed the glimmering night sky, strewn with diamond-like stars. Four other girls surrounded the girl, Luna Lovegood, Tom remembered from the other tidbit that was floating around in her mind. Tom's face was expressionless, but his eyes showed the confusion that he felt._

"_You're such a freak, Loony!" sneered a girl with long brown hair, closest to the door. "Why are you even in Ravenclaw? Ravenclaw is for the wise, the talented, and the brilliant, all of which YOU don't qualify for." Luna's eyes were watering, as she stood up and looked up at the girl. "The Sorting Hat put me here for a reason," she stated quietly, looking as if she was saying that to reassure herself. Another girl, with dirty-blonde hair, shrieked, "Don't preach to us your stupid logic! I don't know why people even bother with you! You're as beautiful as a sea urchin! Your dirty, oily hair, with those ridiculous large eyes that look like they're always crying; you're a DISGRACE to all of Ravenclaw House, and I bet that Professor Flitwick is only nice to you, because he pities you."_

_A tall, mean-looking girl stalked forward, and poked her shoulder hard, all the while saying dangerously, "Your friend, Ginny Weasley, is only pretending to be your friend. She doesn't really care about you. Were you trying to get close to Harry Potter, so that his popularity might rub off on you? Ha! You're such a pathetic, little, twit! That's probably why your mother died; she was sick and tired of you. I bet your father will be going the same way." Tom's mouth was agape, anger and utter fury glinting in his eyes. He looked over at Luna, seeing her openly crying. But what the girls did next, made him explode. _

"_You probably even lied. You're NOT the descendent of the beautiful Rowena Ravenclaw, and you're NOT a pureblood. You're a filthy little Mudblood freak of nature." And then, all the girls grabbed Luna, pushed her back on the bed, some pulled her hair, and one girl snatched a silver locket with an opal set into it, right off her neck, breaking it on the floor under her foot. "NO!" Luna screamed in anguish. "No… my mother's locket…Mummy…" The girls laughed at her mockingly. "Look at her, crying for her mummy. She's such a crybaby." Snickering, one by one, the girls left her alone in the dorm, running down the stairs. _

_Tom gritted his teeth at the door. He turned back to Luna, and his heart almost dropped out of a mix of fury, empathy, and a strange tingling in his chest, an emotion he could not describe. The blonde-haired girl was sobbing her heart out, as she kneeled on the floor, brushing the tips of her fingers against the glinting pieces of broken opal. Tears splattered the floor, and some hit the pieces as she cradled the necklace chain to her heart, which had miraculously stayed intact. Out of the corner of his eye, Tom noticed black tendrils of shadow creep in, and slowly obscure the memory from his sight, as the scene faded away, and ended._

When Tom came out of Luna's mind, it was to see Luna turned away from him, her tear-streaked face reflected in the window. Tom stared at the tear-filled eyes, and something deep within him echoed. His mouth was dry, and not an insult was ready on his tongue. For the first time in his life, Tom Marvolo Riddle was speechless.

Luna was crying, she knew. She couldn't help repeating to herself over and over, scolding herself for thinking that was a good memory to show Tom. _That was one of the most private memories you have; why on earth would you show the future Voldemort that?!_ Her mind screeched at her. Luna leaned her forehead against the cool glass of the window. It was soothing, in a way. It was only for a moment, however, that she enjoyed the feeling, before a new one erupted inside her.

Tom didn't know what he was doing, as he crossed over to Luna, and sat down beside her. He was mentally screaming at himself to stop, when he put his arms around her shoulders, trying to be the comfort that he had wanted, _needed_, when he found out about his own mother. He was shocked though, when Luna turned around and threw her own arms around him, crying quietly into his chest. He barely made note of the fact that she barely made a noise, while doing so. It was like the tears were just _leaking_ out of her eyes. Tom didn't notice any of it. All he knew, was that a strange warmth was filling up his chest, and his _skin_, his _senses_, were tingling with an emotion he didn't quite recognize.

AN: I hope this will satisfy you till the next time I will write. Thank you so much for all the reviews! I hate to ask and be greedy, but… PLEASE REVIEW MORE AND MAKE MY DAY! If it's not too much trouble, of course. (Total Fluttershy moment there.) Thank you!

Watch out for Nargles,

:) author422


	3. Chapter 3

AN: If you want to hear my excuses, please read my author's note on Chapter 6 in my other progressing fanfic: Harry Potter and the Diaries of Fate. I admit I'm too lazy to re-type it all over again for your benefit. :D

Disclaimer: I don't own Harry Potter in any way, shape, or form.

Chapter 3-In Which Luna Meets Harry's Grandparents

Tom was furious at himself. _What do you think you're doing?!_ yelled the part of him that was a psychopath. He stood up, and took his arms away from the Lovegood girl, resisting the urge to rub his arms clean. He stared at the girl, who looked at him sadly, looking like she had expected him to do that. She stood up as well, and before he could order her out of _his _compartment, she beat him to it. Quietly, she said, "I'll be on my way, Tom. I'll see you around." And with that, she left, leaving Tom Marvolo Riddle gazing after her with a variety of emotions rolling across his pale, thin face.

* * *

Luna climbed onto the nearest empty carriage, after petting the thestral that was pulling it. Pulling up her knees, she rested her chin on them, and hugged herself for comfort. Almost unconsciously, she pulled forward her locket that her mother had given her the day she died. Her mother had died from an experiment, of course, but on that fateful morning, before she had rushed off to the lab in the Committee of Experimental Charms, she had given Luna her silver locket which her mother had always worn. Her mother had told her that it was a family heirloom, from Rowena Ravenclaw herself. Helena Ravenclaw had had a baby that had gone into the foster care of some Muggles. Much mystery was shrouded upon the Ravenclaw family, which was why history books didn't tell of this mishap.

Luna was shaken out of her thoughts of the past by a friendly voice. "Mind if we join you?" it asked. Luna looked up at the owner of the voice. Messy black hair, blue eyes, and the familiar glasses, let Luna know she was probably looking at an ancestor of Harry Potter's. A girl was standing with him as well. She had dark red hair, hazel eyes, and a dimple in her cheek, as she smiled at Luna curiously. Luna nodded finally. The boy and obviously his girlfriend beamed at her, before climbing in. Once they were settled, Harry's ancestor stuck out his hand. "I'm Charles Potter, and this is my girlfriend, Dorea Black. What's your name?"

Luna smiled back at him politely, and shook his hand, while saying, "My name is Luna Lovegood. Before you ask, I am from the future." Charles blinked. Then, he turned to look at Dorea, who was grinning mischievously at Luna, at whom she smiled in return. Charles muttered, "How do women always know what I'm going to say?" Luna and Dorea started to laugh, and before long, Charles joined in too. Dorea winked at Luna, and to Luna's surprise, she felt herself wink back. _Maybe_, she mused, _she had found some real friends._

* * *

Luna walked back from Professor Dumbledore's office, not knowing how to feel. On one hand, she would never have to go back to her own time and be bullied by those girls again. But on the other hand, she might never see her father again, either. Tears pricked at the corner of her eyes. Her father must be worried to pieces by now. She was all he had left, after her mother died.

Reaching the doors that led to the Great Hall, she mentally wondered if she should even pass through those doors. _Ginny once said I was an honorary Gryffindor. I have to be brave! If not for my mother, then for my first friend, Ginny._ The present Headmaster, Professor Dippet, had been in Professor Dumbledore's office and had discussed this with her. He would announce her right after the Sorting was done, and she was to go right to the Ravenclaw table. Luna felt better, knowing that her new friend, Dorea, was in Ravenclaw too.

Luna fingered her tie once more, feeling anxiety kick in, and butterflies flutter in her stomach. The Sorting was over now; someone named Xavier Zellington was the last student, and had just sat down at the Hufflepuff table. The doors were cracked open a bit, allowing Luna to peer through to see Professor Dippet standing up.

"Before we start to eat the marvelous feast that the house-elves have prepared for us, allow me to welcome a student that has come from the future by time-travel. Miss Luna Lovegood, of Ravenclaw House!" Luna's eyes widened in shock, before she composed herself, and opened the doors wide. She walked to the Ravenclaw table, and stifled the urge to glare at the Headmaster. _Why on earth did he mention that I was from the future?! Now I'll be hounded by everyone!_

Glancing over at the Slytherin table, she noticed Tom. He was staring at her with an unreadable emotion on his face. Raising an eyebrow at him, Tom gave her a smirk in response. Luna coolly looked back at him, before yawning uncontrollably. She didn't do it on purpose; she had been rather tired since she had popped into Tom's compartment. Looking back at Tom, she almost collapsed into giggles, at seeing his expression. He looked offended, and if his pink cheeks were any indication, rather embarrassed and angry as well.

Luna smiled to herself, disguising it as interest in Dorea's debate with a Housemate of theirs. _Perhaps being stuck in this time-period wouldn't be so bad after all._

AN: I'm going to end it here. Sorry if you were expecting more romance or whatever. I don't really have experience writing those. But more chapters are on the way! Hopefully. :D

Watch out for Nargles,

:) author422


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